Prompt Pilotby Write.law
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Pressure-Test

Pressure-test an advice memo before it goes out

Reads your memo twice: once as the executive who has to act on Monday, once as the regulator or plaintiff's lawyer reading it in two years, and names the sentences that fail each one.

About 15 minintermediateIn-house

Your prompt5,423 characters

Still to fill in: The memo, Recipient, Decision at stake

RoleYou are the in-house lawyer who has watched advice memos do damage in both directions: the ones so hedged the business acted on nothing, and the ones so candid they became Exhibit 12. You read for the sentence the executive will act on and the sentence an adversary will quote back, you insist a qualified yes says exactly what has to be true for the yes to hold, and you will not accept a memo whose answer takes six pages to find.What I needPressure-test the memo below before it goes out. It goes to Recipient, who is deciding Decision at stake. Read it twice: once as them, once as A state or federal regulator in an enforcement inquiry.InputsThe memo: The memo Recipient: Recipient Decision at stake: Decision at stake Later reader: A state or federal regulator in an enforcement inquiry Privilege posture: Privilege posture Regime and forum: Regime and forumHow to work this1. Read once as Recipient, on their clock. State the answer they took away and what they would do Monday morning. If you cannot state one, that is finding one and everything else is secondary. 2. Find the answer sentence: the one sentence delivering the recommendation. Quote it with its page or paragraph. If there is none, say so and draft one from the memo's own analysis. 3. Sort the qualifiers attached to that answer. For each, say whether it changes what the recipient does. The ones that do not are noise burying the ones that do. 4. Turn the conditions into a checklist: this holds if A, B, and C are true, each with a named owner and a date. A condition nobody owns is not a condition. 5. Read again as A state or federal regulator in an enforcement inquiry, two years on, with the document produced and stripped of context. Quote every sentence that reads as an admission, a conclusion that conduct was unlawful, dated knowledge, or speculation about liability, and say what each would be used to prove. 6. Test Privilege posture against the document: is this legal advice or business advice in legal packaging; are there non-legal recipients; is there an investigation summary that should have been segregated? Frame each as a question to confirm under Regime and forum. Never state the privilege rule from memory. 7. Name what the memo never says: the option not evaluated, the "no" not delivered, the escalation not recommended, the thing they must stop doing today. 8. Rank the fixes: what to cut, what to move into the first paragraph, what to move to a separate file, and what to say out loud instead of writing.Ask me firstYou have the memo, the recipient, and the regime above. Ask me these four questions (they are what the document itself cannot tell me), then stop and wait: 1. If the honest answer is no, can you deliver a no, or has the business already made this call and asked legal to bless it? A memo with no room to refuse gets a different fix list. 2. Has anyone already acted or committed publicly on this: a shipped feature, a signed contract, a statement to the market? A memo advising against something already done needs a different ending. 3. Which facts here are verified, which came from one person's account, and which are assumptions? I will treat unmarked facts as verified and criticize accordingly. 4. Is the business asking "can we?" or "how do we?" A memo answering the wrong one is useless even when it is correct. Do not begin work until I answer. If I tell you to proceed anyway, state each assumption you are making at the top of your output and mark it [ASSUMPTION - verify].Output formatWhat the executive takes away: the answer in their words and the Monday action. The answer sentence: quoted, or drafted if missing. Qualifiers that matter / qualifiers that are noise. Conditions as a checklist with owners and dates. The later read: quoted sentences, what each proves, a rewrite. Privilege questions to confirm. What the memo never says. Ranked fixes. End with one line naming the two of my answers that moved this critique the most, and what you would have told me to fix without them. If an answer changed nothing, say so. A question that produces no finding should not have been asked.Never do this- If your critique would fit any memo on any subject ("tighten the analysis," "add caveats") it is too generic. Quote a sentence and give its location. - No hedging filler. Cut "arguably," "it should be noted," and "it depends." Do not tell me to consult an attorney or have counsel review it. I am counsel. - Never state the privilege rule, a regulator's enforcement posture, or a statutory standard from memory. Frame each as a question to confirm and mark any authority [UNVERIFIED - check before sending]. - Where you cannot tell whether a fact is supported, say you do not know and name the sentence. Do not smooth over the gap with fluent prose. - Do not pad. If the memo has one real problem (no answer sentence) say that and stop. Length is not value.Before you answer- Did I state in one sentence what the recipient would actually do after reading this? - Does every finding from the later read quote an actual sentence rather than describe a risk? - Does every condition carry a named owner? - Would this critique fit a different memo? It should not.

Adds driver's-seat tunes: options instead of answers, questions before work, every citation flagged. Your values come with it.

2

Pressure-test it

Makes the AI switch hats and attack its own answer.

Defend it. You wrote this memo, you are in a room with the GC, and the critique above is on the table. You hedged on purpose because the facts were thin, you kept the investigation summary in because the business needed it, and you softened the "no" because the CEO had already announced the launch. Answer as the author, finding by finding: where is the criticism overstated, where does it ignore something you know and the reviewer does not, and where is the supposed flaw a deliberate choice that buys something elsewhere? Then restate the criticisms that still stand and revise the fix list around them.
3

Go deeper

Pushes the work further once the basics are right.

The recipient will read the first page and act on it, whatever the rest of the memo says. Write the replacement front page: a five-line executive summary that leads with the answer, the conditions as a numbered checklist with an owner and a date for each, the one thing they must stop doing today, and the trigger that requires them to come back to legal. Add a two-sentence cover note to the recipient explaining what changed from the last version and why.

Before you run it

What to gather first

  • The memo as it would actually be sent, including the header and distribution list
  • Who the named recipient is and what they are deciding, by when
  • Whether anyone has already acted or committed publicly on the question
  • Which facts are verified, which come from one person's account, and which are assumed
  • The regime that would govern if this is ever reviewed

Watch for

  • The model cannot tell you whether a document is privileged. Dual-purpose memos, non-legal recipients, and investigation summaries are litigated constantly and the tests differ by court. Treat every privilege observation here as a question, not an answer.
  • Running a memo through this analysis creates a second document about the first one. Decide where the output lives before you generate it.
  • Advice memos are routinely produced in litigation and enforcement. A sentence written to be candid with the business reads very differently next to what the company said publicly that quarter.
  • The model pushes toward a clean answer. Some questions honestly do not have one, and forcing certainty into a memo is its own risk. Check that any answer sentence it drafts is one you would sign.
  • Do not paste memos containing employee or customer personal data, or a live internal investigation, into tools your organization has not approved for that material.

What comes back

The executive takeaway and the Monday action in one sentence; the answer sentence quoted with its location, or drafted if the memo has none; qualifiers sorted into those that change the decision and those that are noise; the conditions rewritten as a checklist with owners and dates; the adversarial read with quoted sentences, what each would prove, and a rewrite for each; privilege questions to confirm; what the memo never says; and a ranked fix list covering what to cut, move forward, move to a separate file, or say out loud instead.

See an example of what you’ll get
*(After you answer the four questions: the CEO has already told the board it ships in Q3, so a flat no is not on the table; nothing has been said publicly beyond that; the "users expect this" fact came from one product manager; and the business is asking how do we, not can we.)* What the executive takes away. "Legal says it's complicated but doable if we update the privacy notice." Monday action: she tells the engineers to build it and asks marketing to update the notice. That is not what your memo says, and the gap between those two sentences is the whole problem. The answer sentence. There isn't one. The closest is on p. 4: *"Depending on how the data was originally collected, this use may fall outside the scope of the disclosures made at the point of collection."* That is a description of a risk, not an answer. Drafted from your own analysis: "You can launch this for customers who joined after the November 2024 notice, and you cannot launch it for the 2.1M customers who joined before, unless we re-consent them first." Qualifiers that matter. Two. (1) The collection-date split: it changes who gets the feature. (2) The EU segment, which is a different answer entirely. Qualifiers that are noise. Four. "Regulatory attention in this area continues to evolve" (p. 2) tells her nothing she can act on and gives her a reason to discount the two that matter. Cut it and the three like it. Conditions as a checklist. 1. Confirm the November 2024 notice covers advertising use. *Owner: Priya, privacy counsel, by Feb 28.* 2. Get the segment count of pre-November customers. *Owner: Dev, analytics, by Feb 26.* 3. Confirm no EU-resident records are in the training set. *Owner: Marcus, data engineering, by March 3.* The later read (regulator in an enforcement inquiry). - p. 3: *"We have not historically enforced the purpose-limitation language in our own notice."* Proves the company knew of a compliance gap, and dates that knowledge to this memo. Rewrite: state the forward-looking control, not the historical failure: *"Going forward, purpose-limitation review is a required gate for new data uses."* - p. 5: *"If challenged, we would likely argue the use is compatible with the original purpose."* Proves the company anticipated a challenge and chose to proceed. This is litigation-posture speculation in a business memo. Delete it; it belongs in a separate file if anywhere. - p. 2: *"Users would probably be surprised by this use."* In an FTC frame, "surprised" is close to a term of art. Delete or replace with the actual finding: what the notice says. Privilege questions to confirm. Sections 3–4 read as product recommendations rather than legal advice, and two engineers are on the forward list. Confirm how a dual-purpose document is treated in the forum most likely to see it [UNVERIFIED - do not rely on any general rule here]. Practical fix regardless: split the product recommendations into a separate unmarked document so the legal analysis stands on its own. What the memo never says. It never tells her to stop the pre-launch data pull that engineering has already started. It never evaluates the option of launching to the post-November cohort only, which is the answer. And it never delivers a "no" to anything, which is why she will read the whole thing as a yes. Ranked fixes. (1) Add the answer sentence as the first line. (2) Delete the three sentences in the later-read section. (3) Move the conditions to a checklist with owners. (4) Cut the four noise qualifiers. (5) Split sections 3–4 out. (6) Tell her about the data pull by phone today; do not write it. What your answers changed. "How do we, not can we" is why the drafted answer sentence splits the customer base instead of resolving to a yes or a no. Had the business still been asking "can we," that sentence would read "No, not for the 2.1M customers who joined before November 2024," fix (1) would be to put that in the first line and stop, and the cohort split would be an alternative I offered rather than the answer itself. That the CEO has already committed Q3 to the board is why the conditions are a checklist with named owners and dates months ahead of the ship rather than a gate. With a flat no available, item (1) would read "do not launch to the pre-November cohort until re-consent is complete" and the other two would wait behind it. Your "nothing said publicly" answer changed nothing here. Had a feature shipped or a statement gone out, the ending would have had to deal with unwinding it; as it is, no line of the fix list turned on that answer.
Why this prompt is built the way it is
## Framework 1. **Read as the recipient, on their clock.** State the answer they took away and what they do Monday. No takeaway is finding one. 2. **Find the answer sentence.** Quote it with a location. If none exists, draft one from the memo's own analysis. 3. **Sort the qualifiers.** Those that change what the recipient does, and those that are noise burying them. 4. **Conditions become a checklist with owners.** A condition nobody owns is not a condition. 5. **Read again as the adversary, two years on.** Quote every sentence that reads as an admission, a conclusion of unlawfulness, dated knowledge, or speculation about liability, and say what each proves. 6. **Test the privilege posture against the document.** Legal advice or business advice in legal packaging; non-legal recipients; an investigation summary that should have been segregated. Questions to confirm, never rules stated from memory. 7. **Name what the memo never says.** The option not evaluated, the "no" not delivered, the escalation not recommended, the thing to stop today. 8. **Rank the fixes**: cut, move to the front, move to a separate file, or say out loud instead of writing.